Mistakes in Lovemaking
by MidnightStarr
Summary: Sometimes when you really really think you're prepared, you find out you're really, really not. The not-so-hard way. [nsfw, TysonxHilary]


**MS:** I don't know what this is. My attempt at funny. I don't do good with funny.

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Sex is complicated.

Everyone has troubles with sex. Especially when you and your partner haven't been together that long. There's all kinds of sounds, smells, weird noses, different ideas, worries about how you look and how you taste and how you'll feel... Sex is friggen complicated.

So, before Tyson took the next step with Hilary, he decided he should do some research.

And by _research_ , do not get misconstrued.

Tyson parked his ass in front of the laptop and watched hour after hour after hour, of pornography.

Passionate sex: Check.  
Rough sex: Check.  
Blowjobs: Check.  
Eating out: Check.  
Different positions: Check.  
Toys: Check.  
Hentai: Ch... Well. He thought about it but in the end he left the last one out. Mental note to return later.

By the end of a long 18-hour day in which he'd spent 9 hours in a food coma and the other 9 in a perpetual state of 'soexcitedcan'twaitballsaregettingsobluethisbetterworkout', Tyson felt prepared.

He and Hilary had had the talk a week before. They'd been dating for nearly a year and with that all-important milestone, they both felt that it was due time for them to show their love to one another physically. Were they virgins? No. But they weren't experienced and both of their first times had, as they were each told, ended in disaster.

Tyson remembered that Hilary's story ended with her in tears and an awkward hair in her mouth but honestly, his wasn't much better. He'd been inside for two seconds, smacked his head against hers so bad he ended up with a killer headache and then came so fast that he didn't pull out in time.

Hence: NEW RESOLVE.

The World Champ was not going to disappoint a girl who was truly worth it in bed. Hilary was his first serious girlfriend; sex with her would _matter_. He didn't wanna screw this up.

He would do it right! Just like those tall, beefy guys on RedTube did.

The girls in those videos were screaming a lot, after all. Those dudes must've been doing something right!

...

 _WRONG_.

"Ow! Tyson, slow down!" Hilary had no choice but to speak up and stop him after the fourth time Tyson's fast-paced rhythm resulted in a slick, wet slide of his cock out of her and instead right up against her pelvis. It was starting to hurt and she heard Tyson wince that time as well.

"Damn! Sorry, Hil... Let me go back in." She nodded, figuring that that maneuver must've felt like a broken dick in the making for Tyson as well. What she didn't figure was that Tyson had a back-up plan for his failed 'fuck her so fast she'll have no choice but to cum' technique.

In no time, Hilary let out a surprised squeak as Tyson gripped her by the hips and flipped her onto her stomach. "Tyson, what are you-.." He lifted her at the hips; fixing her into a doggy-style position that would no doubt make things easier.

"Can we try this way?"

Hilary was tempted to say she wanted to have sex face-to-face... But why not. This was new to her too after all, and maybe Tyson would have better luck with his movement back there? She nodded her head. "Okay. Hurry, I... I want you Tyson."

The Champ's movement stilled for a minute, his hand on her right hip stationary before the thoughtfulness and adoration behind Hilary's words really sunk in. He tenderly stroked her skin with his thumb; she always liked it when he did that, said that she was surprised Tyson could be so gentle.

"I want you too, Hilary. I'm going to make you feel really good! I promise." And promise he did. Okay, so maybe Tyson hadn't excelled at the ramming... But back here, the view opened up a whole new doorway to him.

Seriously.

As Tyson bit his bottom lip and pushed back into her, he heard her resounding moan and felt his balls tighten. Of course he had an iron bar on his mind at that point: He was not going to let the floodgates open this early in the night and cum before Hilary had. He really wanted to give her an orgasm... He wanted to show her how much he loved her. Looking down at her, remembering everything he'd learned... Tyson knew just what to try next.

As he rocked into her with a steady rhythm that he was sure she liked, Tyson popped a finger into his mouth and lathered it with spit.

Where that finger went next turned out to be yet another mistake.

The puckered opening her of ass was too available to him. And besides, _all_ of the men in the porn he'd watched had paid their ladies some attention back here! So, finger wet with saliva Tyson pressed the tip against Hilary's opening and tried to press his way inside.

The brunette came to an absolute standstill. " _What_ are you doing?!"

Tyson's hips brought up solid into her own and he pulled his finger back quick as lightning. "Huh? I, I thought we could try this..."

"No way Tyson! Not for our first time!"

Shot down in flames.

He didn't get it... What was he doing wrong?

Regular sex felt awesome. Like, being inside Hilary right now was amazing. But she wasn't screaming...! Hilary didn't seem any closer to cumming now than she had when they first started, and they'd already been at this for almost ten minutes. Everything he'd studied, in everything he watched it seemed like the girl had cum at least once or twice by the fifteen-minute marker. Tyson wasn't even including the time he spent eating her out and the time she'd spent deep-throating his dick!

(Okay, that might be a little off... Tyson thought all girls could do that but they can't and Hilary had hit him pretty hard. She didn't like being choked, apparently.)

Honestly... They'd been off to a rough start since they'd begun.

Now Hilary sort of felt Tyson deflate behind her.

"I'm not very good at this... Am I?"

She blinked her brown eyes and turned over, staring up at Tyson who suddenly felt like Christmas was over as he was removed from her body.

"Tyson... It's our first time, both of us just need to.. Need to calm down and figure each other out."

He shook his head and his dark hair hung in a way that made Hilary realize Tyson was genuinely hurt.

"I'm not making you feel good."

"Yes you are.."

"No, I'm not." The world champ looked utterly indisposed and defeated as he sat backward on his heels with a sigh. Hilary shook her head and she reached out for him, taking Tyson's cheek in her hand. She was no sex genius either, but she wasn't so stupid as to not know that if you didn't keep your man's head in the game, he was gonna lose his hard-on and quick.

"Tyson, I love you. I love that we get to do this... And, and figure out all this stuff together!"

He looked up at her.

"But I keep screwing up..."

"So what? I'm not perfect either!" Her cheeks took on a blush, and this time it was Hilary's turn to look down. "I couldn't make you cum with my mouth..." In that moment all of her insecurities seemed to flood her mind. In the doubtful darkness, Hilary revisited the initial moment that she'd taken her clothes off. She didn't have low self-esteem... Hilary was fairly confident in her appearance. But maybe it was because it was her very first time with Tyson? She was... Nervous. "And, maybe I should've lost a little weight first and wore nicer underwear.."

Things were silent for a long time and when she was starting to wonder if Tyson fell asleep like he so often did, she looked up to find him staring at her like she was insane.

"'Lost weight'? 'Nicer underwear'? You've gotta be joking Hilary." Tyson sighed so heavily that sitting on his heels became sitting on his crossed legs. Reluctantly he grabbed a pillow from the top of the bed and slung it over his lap, covering the hard-on that was suddenly not so hard. "This has nothing to do with how you look… You look perfect."

Her head cocked to the side. "Really…?" Tyson was so rarely… Intimate, and lovingly affectionate with her that sometimes little comments like that still made her blush and Hilary found herself red in the cheeks all over. It made him smile a little; it was kinda hard not to. Even when he was sitting there with a pillow over his cock.

"Really.. It's just about the fact that I can't do anything right."

His words were both wounding and pathetic. Struck a chord somewhere deep inside Hilary's chest and she opened her mouth, closed it, and then opened her mouth again. "Tyson don't talk like that. It's not your fault. You're trying, and we're both new at this! Like I said, we're not going to be perfect… I think, I think it takes a little while for people to get to know exactly what's right to do with-.. The other's body, getting to know them sexually. It's different… And it's a bit intimidating too." Running fingers through her damp brown hair, untangling the small knots that had formed at the back of her neck, Hilary took Tyson's hand and shifted closer to him on the bed.

"Tyson… I love you." Those words always seemed to make his eyes look just a little bit brighter, so once she got the reaction she was looking for, Hilary leaned up and kissed him. "We'll get this right. We were doing good for awhile there too; I'm just a bit too new for-.. Butt-stuff."

The red flash that crossed Tyson's face was instant and both of them couldn't help but giggle. "Really? So my level of suckitude wasn't too off the charts…?"

"Not at all."

Tyson looked down at the fluff covering his dick, and then to Hilary's sun-kissed thigh pressing against his own. He entwined his fingers with hers, leaned down and kissed her again. "I didn't suck so bad that.. That you'd want to give this another go?" He squeezed her hand a little in his. Come on: he was a guy, after all. And when you're sitting naked in the dark with the most beautiful girl in the world, you're gonna get horny. And thank fuck for that because for awhile Tyson was scared he'd literally lost the power; trying to go for the ass when it was their first time having sex…. Was he insane?! Shaking his head, he needed to focus on keeping his blood where it needed to be instead of his cheeks.

"I think that would be best." Tyson's grin was instantly the brightest thing in the room and Hilary laughed a little as he whipped the pillow off of his hips and all but dove into trying to make her lie down. More sloppy kisses as they regained proximity: chest to chest, belly to belly, she felt things would be better this time.

"I promise I'm going to do the best I can this time, I promise I'll do it right! No more stupidity. I am the champion after all." She couldn't help but laugh all over again but slapped at his arm.

" _My_ champion. Let me stay on my hands and knees, this way, it was feeling really good for a few minutes there.." She maneuvered herself the way she wanted to be, Tyson watching with excitement and a cock that stood proud and rearing for its chance at redemption. "I know you'll do it right Tyson, just takes practice. You're not stupid." She was, dare she say it, eager as she felt Tyson rise onto his knees and grip her hips. "It's not like you tried to turn our first time into a porno or anything."

Tyson thanked god and Hilary's awesome ass for small favors. After all, if they tried to do missionary again, Hilary would've seen just how fast her words could defeat a champion's great sword.

 _'...Cock, Tyson... Stop thinking like that. Just because Vlad the Impaler called his dick a great sword doesn't mean you have to.'_

* * *

 **MS:** So, again, I don't know if this really got across what I wanted it to but I was hoping for a cross between funny and weirdly charming...? Sex between first-time partners is often pretty dicey so I wanted to capture that because it's something fanfiction leaves out way too often. But I also wanted to do it in a comedic way. Any good...? Too short? Absolute shit? Review and let me know. This was actually requested by an anonymous Tumblr user a long time ago; I hope I did you justice mysterious friend. 3


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